June 13, 2011Why is it every digital disrupter since Bill Gates and Steve Jobs dresses exactly like Bill Gates and Steve Jobs? We get it, high-tech billionaires. You're too busy innovating to waste any brain cycles on tucking in your shirts. You're so rich and powerful you have absolutely no need to dress to impress. But, honestly, would it kill you to give your cellphone holsters a day off on occasion? And maybe take a gander at Gilt.com while your flunkies are bludgeoning you with PowerPoint presentations? You're the economic leaders of the 21st century and you are not inspiring confidence.

Larry Page, Google

Never wear a shirt that employed more graphic designers than your home page did.

Mark Zuckerberg, Facebook

Facebook Beacon was actually only Zuckerberg’s second worst invention. His first? Business Fleece.

Dick Costolo, Twitter

This shirt is so over capacity in the arms and torso it could fit the #failwhale

Andrew Mason, Groupon

Mason models the answer to the question: Is there anything on the planet so worthless even Groupon can't unload a few thousand SKUs of it at 90 percent off?

Tim Cook, Apple

Stylistically, Steve Jobs left some very tiny shoes to fill at Apple. But Cook's baggy "Reverse Hansbrough" is barely an upgrade to Jobs' perennial toolbag trifecta of Dad jeans, turtlemock, and New Balance 992s.